Hydrochloric Acid → HCID 59599421, compound

HRID 1627552Notes

Reaction equation

HRID 1627552 reaction equation
Cl.O1CCOCC1.C([O:12][C:13](=[O:39])[CH2:14][N:15]1[CH:19]=[C:18]([C:20]2[CH:21]=[N:22][C:23]([NH2:38])=[C:24]([O:26][CH:27]([C:29]3[C:34]([Cl:35])=[CH:33][CH:32]=[C:31]([F:36])[C:30]=3[Cl:37])[CH3:28])[CH:25]=2)[N:17]=[CH:16]1)(C)(C)C>ClCCl>[NH2:38][C:23]1[N:22]=[CH:21][C:20]([C:18]2[N:17]=[CH:16][N:15]([CH2:14][C:13]([OH:39])=[O:12])[CH:19]=2)=[CH:25][C:24]=1[O:26][CH:27]([C:29]1[C:34]([Cl:35])=[CH:33][CH:32]=[C:31]([F:36])[C:30]=1[Cl:37])[CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59599426HCID 59599426, compound

Product 1

HCID 59599421HCID 59599421, compoundYield 108.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 4 M solution of hydrochloric acid in dioxane (0.22 mL, 0.89 mmol) was added to a solution of (4-{6-Amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-imidazol-1-yl)-acetic acid tert-butyl ester (86 mg, 0.18 mmol) in dichloromethane (2 mL). After stirring for two days the reaction was concentrated by rotary evaporation and the residue was dissolved in a minimum amount of methanol. This solution was added dropwise to ether and the resulting mixture allowed to stand overnight. The mixture was filtered and the precipitate was washed with ether and air dried to give (4-{6-Amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-imidazol-1-yl)-acetic acid (83 mg, 93%).

Workup

  1. concentrationwas concentrated by rotary evaporation
  2. dissolutionthe residue was dissolved in a minimum amount of methanol
  3. additionThis solution was added dropwise to ether
  4. waitto stand overnight
  5. filtrationThe mixture was filtered
  6. washthe precipitate was washed with ether and air
  7. customdried

Sources & evidence

ORD record
ord-6ea710d312964970afb0545ce7fffefb
Source dataset
uspto-grants-2014_07
Patent number
US08785632B2

Reaction notes

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